Fondaparinux

Base Information

• Chemical Name: Fondaparinux
• CAS No.: 114870-03-0
• Deprecated CAS: 816468-88-9,119329-39-4,147827-38-1,214767-51-8,393796-46-8,389064-08-8,412015-07-7,129051-67-8,393796-99-1
• Molecular Formula: C₃₁H₄₃N₃O₄₉S₈*10Na
• Molecular Weight: 1728.1
• Hs Code.: 3822000002
• UNII: J177FOW5JL
• DSSTox Substance ID: DTXSID10146903
• Nikkaji Number: J862.320A
• Wikipedia: Fondaparinux
• Wikidata: Q27077698
• NCI Thesaurus Code: C73142
• RXCUI: 321208
• Pharos Ligand ID: PFW37H6H4816
• Metabolomics Workbench ID: 61409
• ChEMBL ID: CHEMBL1201202
• Mol file: 114870-03-0.mol

Synonyms:Arixtra;fondaparinux;fondaparinux sodium;Quixidar

Chemical Property of Fondaparinux

Chemical Property:

• PSA: 900.82000
• LogP: -9.34120
• Storage Temp.: 2-8°C
• Solubility.: Water
• XLogP3: -14.7
• Hydrogen Bond Donor Count: 19
• Hydrogen Bond Acceptor Count: 52
• Rotatable Bond Count: 30
• Exact Mass: 1506.9513344
• Heavy Atom Count: 91
• Complexity: 3450

Purity/Quality:

99% ^*data from raw suppliers

FondaparinuxSodium ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antithrombotic Agents
• Canonical SMILES: COC1C(C(C(C(O1)COS(=O)(=O)O)OC2C(C(C(C(O2)C(=O)O)OC3C(C(C(C(O3)COS(=O)(=O)O)OC4C(C(C(C(O4)C(=O)O)OC5C(C(C(C(O5)COS(=O)(=O)O)O)O)NS(=O)(=O)O)O)O)OS(=O)(=O)O)NS(=O)(=O)O)O)OS(=O)(=O)O)O)NS(=O)(=O)O
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COS(=O)(=O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](O2)C(=O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COS(=O)(=O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O[C@@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COS(=O)(=O)O)O)O)NS(=O)(=O)O)O)O)OS(=O)(=O)O)NS(=O)(=O)O)O)OS(=O)(=O)O)O)NS(=O)(=O)O
• Recent ClinicalTrials: Superficial Vein Thrombosis (SVT) Treated With Rivaroxaban Versus Fondaparinux
• Recent EU Clinical Trials: A Multicenter, Adaptive, Randomized Controlled Platform Trial of the Safety and Efficacy of Antithrombotic Strategies in Hospitalized Adults with COVID-19
• Recent NIPH Clinical Trials: Laboratory monitoring and the anti-coagulant effect of Fondaparinux after total knee arthroplasty
• Description: Fondaparinux sodium was first introduced in the US for prophylaxis of deep vein thrombosis which may lead to pulmonary embolism following major orthopaedic surgery. Fondaparinux is the first of a new class of antithrombic agents distinct from low molecular weight heparin (LMWH) and heparin. This entirely synthetic molecule is a copy of the heparin pentasaccharide sequence, the shortest fragment able to catalyze antithrombin lllmediated inhibition of factor Xa thereby inhibiting thrombin generation without antithrombin action. Fondaparinux does not display significant effects on coagulation tests (such as activated partial thromboplastin time and prothrombin time), does not bind to platelet factor 4 or promote heparin-induced thrombocytopenia. In phase III studies, fondaparinux significantly reduced the incidence of thromboembolism following orthopedic surgery, with an overall risk reduction of 50% in comparison to the LMWH, enoxaparin. Following subcutaneous administration, fondaparinux has a nearly complete bioavailability, a rapid onset of action, a prolonged half-life (17.2 h) enabling once daily dosing and is not metabolized preceeding renal excretion. The drug appears to be generally safe, with haemoragic complications either comparable to or higher than those for LMWH.
• Uses: Fondaparinux sodium has been used to test its neutralizing effect towards enterovirus D68-947 infection. It may be used in ultraviolet photodissociation (UVPD) measurements. Synthetic pentasaccharide corresponding to the anti-thrombin binding site of heparin. Anti-thrombotic.
• Clinical Use: Prophylaxis of deep vein thrombosis Treatment of deep vein thrombosis, pulmonary embolism, unstable angina and after a myocardial infarction
• Drug interactions: Potentially hazardous interactions with other drugs Increased risk of bleeding in combination with any other drugs that affect coagulation.

Technology Process of Fondaparinux

There total 1 articles about Fondaparinux which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methyl O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-O-(2-azido-2-deoxy-3,6-di-O-sulfo-α-D-glucopyranosyl)-(1->4)-O-(methyl 3-O-benzyl-2-O-sulfo-α-L-idopyranosyl.. → methyl O-(2-deoxy-2-sulfamido-6-O-sulfo-α-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->4)-O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-α-D-glucopyranosyl)-(1->4)-O-(2-O-sulfo-α-L-idopyranosyluronic acid)-(1->4)-2-deoxy-2-sulfamido-6-O... (114870-03-0,115997-33-6)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/S0008-6215(00)90842-5

Refernces